A novel synthesis of ( Z)-2-(1-trimethylgermyl-1-alkenyl)-1,3,2-dioxaborinanes and their conversion into carboxylic acids

Abstract

A novel procedure for preparing heterocyclic compounds such as ( Z)-2-(1-trimethylgermyl-1-alkenyl)-1,3,2-dioxaborinanes based on 1-trimethylgermyl-1-alkynes is described. 1-Trimethylgermyl-1-alkynes easily obtainable by deprotonation of 1-alkynes with n-butyllithium followed by treatment with trimethylgermanium chloride, are readily hydroborated in n-pentane in the presence of boron trichloride in hexane at 0 °C for 3 h. The resulting supernatant clear solution was separated from boron trichloride–methyl sulfide complex. It was then reacted with 1,3-propane diol at 0 °C for 0.5 h. The resulting representative ( Z)-2-(1-trimethylgermyl-1-alkenyl)-1,3,2-dioxaborinanes were isolated in good yields (65–86%) and in high stereochemical purities (>98%) as evidenced by NMR spectral data. The carbon skeletons present in these intermediates were confirmed by alkaline hydrogen peroxide oxidation to the corresponding carboxylic acids.